Detection and Quantification of Sulfated Disaccharides from Keratan Sulfate and Chondroitin/Dermatan Sulfate during Chick Corneal Development by ESI-MS/MS

Zhang, Yuntao; Conrad, Abigail H.; Tasheva, Elena S.; An, Ke; Corpuz, Lolita M.; Kariya, Yutaka; Suzuki, Kiyoshi; Conrad, Gary W.

doi:10.1167/iovs.04-1453

Cited by 45 publications

(38 citation statements)

References 45 publications

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“…7C). The presence in the CID spectrum of Y 1 with m/z ϭ 377, Z 1 with m/z ϭ 359, and B 1 with m/z ϭ 157, and lack of the diagnostic product ion for D2a0 (18,34) show that the predominant and perhaps only species eluting at this position has sulfate on the hexosamine side of the glycosidic bond. C. elegans chondroitin consists entirely of D0a0, as described previously (3,35,36).…”

Section: Quantitative Disaccharide Analysismentioning

confidence: 99%

Evolutionary Differences in Glycosaminoglycan Fine Structure Detected by Quantitative Glycan Reductive Isotope Labeling

Lawrence

Olson

Steele

et al. 2008

Journal of Biological Chemistry

175

195

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To facilitate qualitative and quantitative analysis of glycosaminoglycans, we tagged the reducing end of lyase-generated disaccharides with aniline-containing stable isotopes ( 12 C 6 and 13 C 6 ). Because different isotope tags have no effect on chromatographic retention times but can be discriminated by a mass detector, differentially isotope-tagged samples can be compared simultaneously by liquid chromatography/mass spectrometry and quantified by admixture with known amounts of standards. The technique is adaptable to all types of glycosaminoglycans, and its sensitivity is only limited by the type of mass spectrometer available. We validated the method using commercial heparin and keratan sulfate as well as heparan sulfate isolated from mutant and wild-type Chinese hamster ovary cells, and select tissues from mutant and wild-type mice. This new method provides more robust, reliable, and sensitive means of quantitative evaluation of glycosaminoglycan disaccharide compositions than existing techniques allowing us to compare the chondroitin and heparan sulfate compositions of Hydra vulgaris, Drosophila melanogaster, Caenorhabditis elegans, and mammalian cells. Our results demonstrate significant differences in glycosaminoglycan structure among these organisms that might represent evolutionarily distinct functional motifs.Metazoans make several types of sulfated glycosaminoglycans (GAGs), 2 including keratan sulfate (KS), chondroitin sulfate/dermatan sulfate (CS/DS), and heparan sulfate/heparin (HS). Each type of chain consists of unique disaccharide units. KS consists of galactose (Gal) and GlcNAc ([Gal␤1, 4GlcNAc␤1,3] n ) with variable sulfation at C6 of either sugar. CS/DS assembles as a copolymer of GlcA␤1,3GalNAc␤1,4 and then undergoes various processing reactions, including C5 epimerization of a portion of GlcA units to iduronic acid in DS, O-sulfation at C2 and more rarely at C3 of the uronic acids, and O-sulfation at C4 and C6 of the GalNAc residues (1). HS is the most highly modified GAG, consisting initially of GlcA␤1,4GlcNAc␣1,4 units, which then undergo variable processing by GlcNAc N-deacetylation and N-sulfation, C5 epimerization of some GlcA units to iduronic acid, and O-sulfate addition to C2 of the uronic acids and C6 and more rarely at C3 of the glucosamine units (2). The arrangement of the modified residues along the chain creates binding sites for numerous growth factors, enzymes, and extracellular matrix proteins. The structural variation that can occur makes sulfated GAG chains one of the most complex classes of macromolecules found in nature.GAG fine structure is typically assessed by analyzing the disaccharide composition of an isolated mixture of chains. A number of techniques have been developed to accomplish this task that rely on chemical or enzymatic depolymerization of the chains into their constituent disaccharides, followed by separation via anion exchange chromatography, reversed-phase chromatography with ion pairing agents, or capillary electrophoresis. These techniques separate...

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Section: Quantitative Disaccharide Analysismentioning

confidence: 99%

Evolutionary Differences in Glycosaminoglycan Fine Structure Detected by Quantitative Glycan Reductive Isotope Labeling

Lawrence

Olson

Steele

et al. 2008

Journal of Biological Chemistry

175

195

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“…Chondroitin B is no longer classified as CS. C6S is distributed in the growth plates (increasing from the proliferative zone to the hypertrophic zone, Ling et al 1996), aorta (Yasuda et al 2013), and cornea (Zhang et al 2005). C6S has been identified in pathological states, including (1) contributing to arterial retention of cholesterolrich, atherogenic lipoproteins (Mourão et al 1981), a key event that initiates atherosclerosis (Williams and Tabas 1995), (2) accumulating in the connective tissue stroma of human colon carcinomas (Adany et al 1990), and (3) excessive secretion of total CS in urinary excretions of MPS IVA and VII patients, although C4S and C6S are not clearly separate (semiquantitative) (Hopwood and Harrison 1982;Hata and Nagai 1972;Haskins et al 1984).…”

Section: Discussionmentioning

confidence: 99%

Chondroitin 6-sulfate as a novel biomarker for mucopolysaccharidosis IVA and VII

Kubaski

Shimada

Tomatsu

et al. 2015

Molecular Genetics and Metabolism

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Chondroitin 6-sulfate (C6S), a glycosaminoglycan (GAG), is distributed mainly in the growth plates, aorta, and cornea; however, the physiological function of C6S is not fully understood. One of the limitations is that no rapid, accurate quantitative method to measure C6S has been established. Mucopolysaccharidosis IVA and VII (MPS IVA and VII) are caused by the deficiency of N-acetylgalactosamine-6-sulfate sulfatase and b-D-glucuronidase, respectively, resulting in accumulation of C6S and other GAG(s). While levels of keratan sulfate (KS), heparan sulfate, and dermatan sulfate in samples from MPS patients are well described, this is the first report of quantitative analysis of C6S levels in samples from MPS IVA and VII patients.We developed a method to digest polymeric C6S and measure resultant disaccharides using liquid chromatographytandem mass spectrometry (LC-MS/MS). C6S levels were measured in the blood from control subjects and patients with MPS IVA and VII aged from 0 to 58 years of age. We also assayed KS levels in the same samples for comparison with C6S.Levels of C6S in the blood decreased with age and were significantly elevated in patients with MPS IVA and VII, compared with age-matched controls. Levels of KS in patients with MPS IVA were also higher than those in agematched controls, although differences were less pronounced than with C6S. Combining KS and C6S data, discriminated patients with MPS IVA from age-matched control subjects were better than either C6S or KS levels alone.In conclusion, this first report showing that blood levels of C6S are quantitatively evaluated in patients with MPS IVA and VII indicates that C6S could be a useful biomarker for these metabolic disorders.

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“…The flow rate was 0.7 mL/min, and the gradient was as follows: 0 min 100% solution A, 1 min 70% solution A, 2 min 70% solution A, 2.20 min 0% solution A, 2.60 min 0% solution A, 2.61 min 100% solution A, 5 min 100% solution A. The mass spectrometer was operated with electrospray ionization in the negative ion mode (Agilent Jet Stream technology) with drying gas temperature 350 °C, drying gas flow 11 L/min, nebulizer pressure 58 psi, sheath gas temperature 400 °C, sheath gas flow 11 L/min, capillary voltage 4,000 V, nozzle voltage 2,000 V. Specific precursor and product ions, m/z, were used to quantify each disaccharide respectively (IS,354.3,193.1;DS,378.3,175.1;462,97;462;138;175.1) (Oguma et al, 2007;Zhang et al, 2005;Saad et al, 2005;Wei et al, 2011). DS was measured as Di-0S after digestion of Di-4S by a 4S-sulfatase present in the preparation of chondroitinase B.…”

Section: Lc-ms/msmentioning

confidence: 99%

Newborn screening for mucopolysaccharidoses: a pilot study of measurement of glycosaminoglycans by tandem mass spectrometry

Kubaski

Mason

Nakatomi

et al. 2017

Molecular Genetics and Metabolism

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Detection and Quantification of Sulfated Disaccharides from Keratan Sulfate and Chondroitin/Dermatan Sulfate during Chick Corneal Development by ESI-MS/MS

Abstract: New, rapid, direct chemical analysis of extracellular matrix components obtained from sections from embryonic and adult chick corneas reveals heretofore undetected changes in sulfation characteristics of KS and CS/DS disaccharides during corneal development.

Cited by 45 publications

References 45 publications

Evolutionary Differences in Glycosaminoglycan Fine Structure Detected by Quantitative Glycan Reductive Isotope Labeling

Evolutionary Differences in Glycosaminoglycan Fine Structure Detected by Quantitative Glycan Reductive Isotope Labeling

Chondroitin 6-sulfate as a novel biomarker for mucopolysaccharidosis IVA and VII

Newborn screening for mucopolysaccharidoses: a pilot study of measurement of glycosaminoglycans by tandem mass spectrometry

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